Methods and systems for producing isosorbide from biomass

Abstract

Methods and systems for producing isosorbide from biomass are disclosed. In one embodiment, a method of producing isosorbide from biomass may include contacting biomass, a catalyst mixture of a noble metal and a first solid acid, and hydrogen to form a first reaction mixture, and heating the first reaction mixture to form at least one intermediate compound. Further, the intermediate compound is contacted with a second solid acid to form a second reaction mixture, and heating the second reaction mixture to form isosorbide.

1 . A method of producing isosorbide from a biomass, the method comprising:
 contacting biomass, a catalyst mixture of a noble metal and a first solid acid, and hydrogen to form a first reaction mixture;   heating the first reaction mixture to form at least one intermediate compound;   contacting the at least one intermediate compound with a second solid acid to form a second reaction mixture;   heating the second reaction mixture to form isosorbide; and   isolating the isosorbide.   
     
     
         2 . The method of  claim 1 , wherein contacting the biomass comprises contacting a carbohydrate, polysaccharide, monosaccharide, disaccharide, cellulose, lignin, starch, pentose, or any combination thereof. 
     
     
         3 . The method of  claim 1 , wherein heating the first reaction mixture comprises heating to form a depolymerization product of biomass selected from a monosaccharide, a disaccharide, sorbitol, sorbitan, or any combination thereof 
     
     
         4 . The method of  claim 1 , further comprising removing the catalyst mixture from the at least one intermediate compound prior to contacting the at least one intermediate compound with the second solid acid. 
     
     
         5 . The method of  claim 1 , wherein contacting the catalyst mixture comprises contacting the catalyst mixture comprising a noble metal including Au, Pt, Pd, Ir, Os, Ag, Rh, Ru, or any combination thereof. 
     
     
         6 . The method of  claim 1 , wherein contacting the catalyst mixture comprises contacting a first solid acid including a metal oxide, a metal halide, a metal sulfate, a metal phosphate, zeolite, an ion-exchange resin, or any combination thereof 
     
     
         7 . The method of  claim 1 , wherein contacting the catalyst mixture comprises contacting with a catalyst mixture including ZrO 2 (SO 4 ) 2 , TiCl 3 , Ti 2 (SO 4 ) 3 , CrPO 4 , CrCl 2 , MnCl 2 , Mn 3 (PO 4 ) 2 , Co 3 (PO 4 ) 2 , CoSO 4 , MoO 3 , Mo(SO) 3 , TaF 5 , W(PO) 4 , Al 2 O 3 , NbOPO 4 , Nb 2 O 5 , NbSO 4 , TaCl 2 , TaSO 4 , Ta 3 PO 4 , SnPO 4 , SnCl 2 , SnSO 4 , VCl 2 , VPO 4 , VSO 4 , ZnSO 4 , ZnCl 2 , ZnPO 4 , NbSiO 2 , or any combination thereof. 
     
     
         8 . The method of  claim 1 , wherein contacting the catalyst mixture comprises contacting with the catalyst mixture including a noble metal present in the first reaction mixture at a concentration of about 0.1% to about 10% by weight. 
     
     
         9 . The method of  claim 1 , wherein contacting the catalyst mixture comprises contacting with the catalyst mixture including a first solid acid present in the first reaction mixture at a concentration of about 0.1% to about 10% by weight. 
     
     
         10 . The method of  claim 1 , wherein contacting the catalyst mixture comprises contacting with Pt/Zeolite, Ru/Al 2 O 3 , Ru/NbOPO 4 , Pd/ZrOSO 4 , Pt/Nb 2 O 5 , Pd/WO 3 , or any combination thereof 
     
     
         11 . The method of  claim 1 , wherein heating the first reaction mixture comprises heating to a temperature of about 140° C. to about 190° C. 
     
     
         12 . The method of  claim 1 , wherein heating the first reaction mixture comprises heating for about 12 hours to about 36 hours. 
     
     
         13 . The method of  claim 1 , wherein heating the first reaction mixture comprises heating under a hydrogen pressure of about 2 MPa to about 6 MPa. 
     
     
         14 . The method of  claim 1 , wherein heating the first reaction mixture comprises heating to a temperature of 170° C. for 24 hours under a H 2  pressure of 4 MPa. 
     
     
         15 . The method of  claim 1 , wherein contacting with the second solid acid comprises contacting with the second solid acid catalyst present in the second reaction mixture at a concentration of about 0.1% to about 10% by weight. 
     
     
         16 . The method of  claim 1 , wherein contacting with the second solid acid catalyst comprises contacting with ZrO(SO 4 ), TiCl 3 , Ti 2 (SO 4 ) 3 , CrPO 4 , CrCl 2 , MnCl 2 , Mn 3 (PO 4 ) 2 , Co 3 (PO 4 ) 2 , CoSO 4 , MoO 3 , Mo(SO) 3 , TaF 5 , W(PO) 4 , Al 2 O 3 , NbOPO 4 , Nb 2 O 5 , Nb SO 4 , TaCl 2 , TaSO 4 , Ta 3 PO 4 , SnPO 4 , SnCl 2 , SnSO 4 , VCl 2 , VPO 4 , VSO 4 , ZnSO 4 , ZnCl 2 , ZnPO 4 , NbSiO 2 , or any combination thereof. 
     
     
         17 . The method of  claim 1 , wherein heating the second reaction mixture comprises heating to a temperature of about 210° C. to about 250° C. 
     
     
         18 . The method of  claim 1 , wherein heating the second reaction mixture comprises heating for about 12 hours to about 36 hours. 
     
     
         19 . The method of  claim 1 , wherein heating the second reaction mixture comprises heating to a temperature of about 230° C. for 18 hours in the presence of ZrO 2 (SO 4 ) 2  catalyst. 
     
     
         20 . The method of  claim 1 , wherein isolating the isosorbide comprises extracting isosorbide from the second reaction mixture with xylene or ethyl acetate. 
     
     
         21 . The method of  claim 1 , wherein an isosorbide yield is about 45% to about 70%. 
     
     
         22 . The method of  claim 1 , wherein the method is performed in a batch reactor or a continuous flow reactor. 
     
     
         23 . A reactor system comprising:
 one or more reaction vessels configured to heat a first reaction mixture to a first heating condition, and a second reaction mixture to a second heating condition,   wherein the first reaction mixture comprises a biomass, a catalyst mixture of a noble metal and a first solid acid, and hydrogen, and   the second reaction mixture comprises degradation products of the biomass and a second solid acid.   
     
     
         24 . The reactor system of  claim 23 , wherein the reactor system is a batch reactor system or a continuous flow reactor system. 
     
     
         25 . The reactor system of  claim 23 , wherein the reactor system is configured to produce isosorbide from biomass and H 2 . 
     
     
         26 . The reactor system of  claim 23 , wherein the first heating condition comprises heating to a temperature of about 140° C. to about 190° C. for about 12 hours to about 36 hours. 
     
     
         27 . The reactor system of  claim 23 , wherein the second heating condition comprises heating to a temperature of about 210° C. to about 250° C. for about 12 hours to about 36 hours. 
     
     
         28 . The reactor system of  claim 23 , wherein the reaction vessel is configured to maintain a H 2  pressure of about 2 MPa to about 6 MPa in the reactor vessel. 
     
     
         29 . The reactor system of  claim 23 , wherein the catalyst mixture in the first reaction mixture comprises Pt/Zeolite, Ru/Al 2 O 3 , Ru/NbOPO 4 , Pd/ZrOSO 4 , Pt/Nb 2 O 5 , Pd/WO 3 , or any combination thereof. 
     
     
         30 . The reactor system of  claim 23 , wherein the solid acid in the second reaction mixture comprises ZrO 2 (SO 4 ) 2 , NbOPO 4 , Al 2 O 3 , or any combination thereof. 
     
     
         31 . The reactor system of  claim 23 , further comprising a thermoelectric couple, a pressure gauge, a temperature controller, a cooling system, a mechanical stirrer, or any combination thereof.